Senior Benefits Specialist

Hi, we’re TechnologyAdvice. At TechnologyAdvice, we pride ourselves on helping B2B tech buyers manage the complexity and risk of the buying process. We are a trusted source of information for tech buyers, delivering advice and facilitating connections between our buyers and the world’s leading sellers of business technology. Headquartered in Nashville, Tennessee, we are a remote-first company with more than 20 digital publications and over 500 global team members in the US, UK, Singapore, Australia, and the Philippines. We’re proud to have been repeatedly recognized as one of America’s fastest growing private companies by Inc., as well as a Tennessee top workplace. We work hard each day and have fun, too, with monthly virtual events, recreational slack channels, and the occasional costumed dance from our CEO. All positions are open to remote work unless otherwise specified in the requirements below. The opportunity We are seeking a Senior HR Generalist (Benefits Focus) to join our People Operations team in the Philippines. This role will support a wide range of HR functions while serving as the primary point of contact for benefits administration and employee support across multiple regions, with a strong emphasis on the United States. The ideal candidate will have comprehensive HR experience paired with in-depth knowledge of US benefits administration and compliance. Familiarity with UK benefits programs or other international markets is a strong plus. This position requires a highly organized, detail-oriented, and collaborative HR professional who can balance day-to-day HR operations with strategic benefits initiatives. The ideal candidate will be a hands-on, detail-oriented HR professional with strong knowledge of U.S. benefits regulations and compliance requirements and the ability to collaborate effectively across regions. Employment Level: Mid Level Employment Type: Full Time Location: Philippines Working Hours: 9pm to 6am PHT (APR-OCT) or 10pm to 7am PHT (NOV-MAR) What you'll do Administer and manage U.S. employee benefits programs, including medical, dental, vision, life insurance, disability, retirement (401k), wellness initiatives, and other perks. Partner with brokers, carriers, and vendors to oversee open enrollment, renewals, enrollments, billing, and benefit communications. Support benefits administration in the Philippines, UK, and APAC, ensuring compliance with local labor laws and alignment with global best practices. Serve as the primary point of contact for employee benefits inquiries, life event changes, and claims resolution, delivering timely and professional support. Collaborate with payroll and HR to ensure accurate deductions, reporting, and recordkeeping. Monitor benefits utilization, costs, and trends, providing insights and recommendations to HR leadership on program performance and competitiveness. Research, benchmark, and recommend market-competitive benefits and recognition programs to enhance the global employee experience and strengthen total rewards strategy. Ensure compliance with U.S. federal and state laws (ERISA, ACA, HIPAA, COBRA) and applicable international regulations. Develop and maintain clear, employee-friendly benefits documentation and communications. Support core HR functions such as onboarding, offboarding, policy updates, and compliance, contributing to continuous process improvement across People Operations. Perform other related duties and projects as assigned. Who you are 5+ years of HR experience, with at least 3 years focused on U.S. benefits administration. Experience with UK and APAC regional benefits programs is a plus. Strong understanding of US compliance requirements (ERISA, ACA, COBRA, HIPAA, etc.). Experience working with benefits brokers, carriers, and HRIS/benefits platforms. Experience working with HRIS and benefits administration systems. Excellent attention to detail, organizational skills, and ability to handle confidential information. Strong interpersonal and communication skills, with the ability to support employees across diverse cultures and time zones. Strong analytical, organizational, and problem-solving skills. Must have a working laptop/pc and internet and back-up connection. Agile professional who excels in a fast-paced environment and thrives on continuously pivoting strategies to drive business needs forward. **The duties and responsibilities listed above describe the post as it is in general terms and are not definitive. The job holder is expected to accept any reasonable alterations that may from time to time be necessary. ** What we offer you Career Growth: Advance with mentorship programs, leadership academies, and opportunities to shape company culture and DEI initiatives. Flex Fridays: Adjust your 40-hour week to enjoy a full or half day off on Fridays. Remote-First Culture: Work from the comfort of your home. Paid Time Off: Enjoy 14 days of annual paid time off, plus all regular Philippine government-declared holidays to unwind and recharge. Plus 5 additional days after 1 year. Comprehensive Coverage: Full enrollment in Philippine statutory benefits: SSS, PhilHealth, and HDMF. Healthcare: Healthcare reimbursement to help ensure you are covered. De Minimis Allowance: Enjoy a monthly rice subsidy, following government guidelines. Wellness Perks: Access the Headspace app to support your well-being. Speaker Series Bonus: Present in our monthly speaker series and earn a bonus. #LI-Remote Work authorization Employer work visa sponsorship and support are not provided for this role. Applicants must be currently authorized to work in the Philippines at hire and must maintain authorization to work in the Philippines throughout their employment with our company. Salary Range We seek to hire top-tier individuals and intend for our compensation to be at a rate that allows us to recruit and retain individuals who align with our core values, purpose, mission, and vision. Final total compensation is based on a multitude of factors including, but not limited to, skill level, relevant experience to the position, and cost of labor. Monthly Pay Range ₱75,000—₱83,000 PHP EOE statement We believe that our differences make us stronger, and thus foster a diverse and inclusive culture where people feel safe being themselves. TechnologyAdvice is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, age, religion, sex, national origin, disability, protected veteran status, or any other characteristic protected under federal, state or local law. Pre-employment screening required. TechnologyAdvice does not engage with external staffing agencies. Any candidates introduced by such firms will not be eligible for compensation. TechnologyAdvice communicates only through @technologyadvice.com emails and official recruiting platforms. We never recruit via Teams, WhatsApp, or similar apps, and we will never request money, gift cards, or personal financial details during hiring. Any AI-generated or incomplete application answers will be auto-rejected.